27 Best Hipster Outfits for Men & Women in 2020

It seems like ages ago that “hipster” became a part of the fashion zeitgeist — after all, the original hipsters have their roots in the 1940s — but it was really in the late 2000s and 2010s that “hipster” started to become a household word.

Love it or hate it, hipster subculture brings with it a distinct set of fashions, and many of them are quite pleasing to the eye. If you’re looking to take on a style that is hipster-inspired, we’re not here to judge you — in fact, we’re here to help you get on the right path with great outfit ideas.

Hipster Outfits for Men

1. Casual Hipster Outfits

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Nextluxfashion 20200525 Joshsavesmoney 20200102 I61kza
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Nextluxfashion 20200526 Arthemonlis 20200116 Vuchvl
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Nextluxfashion 20200526 Chriisguz 20190907 Lzxkqi
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Nextluxfashion 20200526 The Outdoor Runner 20180908 Vaiirx
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Nextluxfashion 20200528 Sahibaz 20200429 Iunam5
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We have good news for those who fancy themselves a casual dresser — hipster style is, at its very core, casual. In fact, some of the most iconic hipster wardrobe pieces include the flannel plaid shirt, the denim button-up, and, of course, a nice pair of tapered jeans.

Just because you’re kickin’ it casual doesn’t mean that you can’t dress with intention, though. An added accessory like a wristwatch or beanie can really pull a hipster outfit together.


2. Hipster Party Outfits

Hipster Party Outfit Marcko Lucatero
Source: @marcko_lucatero via Instagram
Hipster Party Outfit Mr.arnold Lit
Source: @mr.arnold_lit via Instagram

The biggest things hipsters are known for, aside from their bicycles and vinyl records, might be their house parties. And one case of PBR does not a hipster house party make — to truly party like a hipster, you need to know how to party in style. To easily add these elements of style, try pushing out of your comfort zone a bit with a wide-brimmed hat, a leather jacket, or even suspenders.


3. Spring Hipster Outfits

Spring Hipster Outfit Lebza Direko
Source: @lebza_direko via Instagram
Spring Hipster Outfit Sdelail
Source: @sdelail via Instagram

Although some pundits may claim that all hipster fashion choices blend into one another, there are distinct seasonal trends in the world of hipster clothing. To quickly put together an outfit that screams spring, invest in a light textured light jacket (jean or corduroy material is great), a solid pair of ankle boots (leather or suede works great), and a pair of comfortable jeans (ripped skinny jeans if you’re feeling adventurous).


4. Summer Hipster Outfits

Summer Hipster Outfit Lebarbudo
Source: @lebarbudo via Instagram

Although summer may be the season that calls for the least amount of clothing, there are still creative things that can be done to put together a hipster-inspired outfit.

When it comes to style fit for the sunshine, floral patterns are a must. Denim shorts are also a solid choice, though a pair of trousers made from breathable fabric will also do a trick if you’re just not much into shorts.


5. Vintage Hipster Outfits

Vintage Hipster Outfit Dieumagnifique
Source: @dieumagnifique via Instagram
Vintage Hipster Outfit Imbigdashehzada
Source: @imbigdashehzada via Instagram
Vintage Hipster Outfit Keiser.925
Source: @keiser.925 via Instagram
Vintage Hipster Outfit Magoplip
Source: @magoplip via Instagram
Vintage Hipster Outfit Mr.marionel
Source: @mr.marionel via Instagram
Vintage Hipster Outfit Rustyjamesman
Source: @rustyjamesman via Instagram

Shopping vintage is deeply ingrained in hipster culture, but it takes a certain amount of practice before you have a true eye for old-fashioned treasures.

Even if you’re not one for thrift store shopping, you can pull off a blast from the past by incorporating fashion items like acid-washed jeans, sneakers from the 90s, a distressed denim jacket, and clothing items with a plaid pattern.


6. Winter Hipster Outfit

Vintage Hipster Outfit Cityofpinesofficial
Source: @cityofpinesofficial via Instagram

To assemble the perfect winter outfit that appeals to all of your hipster sensibilities, embrace the magic of simple but effective wardrobe items like chunky turtlenecks, long, solid-colored turtlenecks, and long-sleeved button-ups. The winter season is also a great time to show off your taste in boots. Not only will a trendy pair of boots keep your feet warm and dry, but it can really pull an outfit together, too.


Hipster Outfits for Women

1. Casual Hipster Outfits

Casual Hipster Outfit Flowerpufffgirl
Source: @flowerpufffgirl_ via Instagram

For the hipster girl looking to keep things casual, there are some tried and true ways to pull a look off. First of all, whether it’s on a blouse, shirt, or skirt, stripes are your friend. Plaid patterns are also effective at checking off all of the stylish and casual boxes, and work great both as a jacket or button-up. Some black jeans can give your outfit an edgier look. A casual occasion is also the perfect time to show off your favorite pair of sneakers (Converse, anyone?)


2. Hipster Party Outfits

Hipster Pary Outfit Gypsyhairartist
Source: @gypsyhairartist via Instagram

The hipster look lends itself well to a party atmosphere, and this is incredibly true for female fashionistas. Hipster vibes are casual all around, so one of the best ways to go about dressing for a party is to accessorize a casual outfit. While it may seem intimidating on the surface, this can easily be done with a fancy glitch and a pair of subtle but pretty heels.


3. Spring Hipster Outfits

Spring Hipster Outfit S.priite
Source: @s.priite via Instagram
Spring Hipster Outfit Simonsaidd
Source: @simonsaidd via Instagram

The springtime is one of the best times to show off all of the shades of your wardrobe. To do it in the style of hipsterdom, women can look for soft tones like pastels, or even light grays and browns. Spring weather is also well-suited to a trendy pair of jeans, whether they be bootcut, skinny, or boyfriend style. Of course, feel free to polish your outfit off with a pair of combat boots.


4. Summer Hipster Outfits

Casual Hipster Outfit Alenabule
Source: @alenabule via Instagram

It can be difficult to dress for warm weather, but with a little creativity, you can wear some of your best outfits in the warmest months of the year. Sunny days calls for seldom-seen wardrobe items like skirts, shorts, and sandals. Favored patterns that are fit for warm weather include cheetah or leopard print, stripes, and vibrant geometric patterns.


5. Vintage Hipster Outfits

Vintage Hipster Outfit Rinatsolomon Stylist
Source: @rinatsolomon_stylist via Instagram
Vintage Hipster Outfit Wehatehipsters
Source: @wehatehipsters via Instagram

Could it be that hipsters are onto something with their eye for vintage fashion? There is nothing outdated about fashion choices that include the likes of pleather pants, distressed jeans, and a tartan shirt. By being bold and mixing and matching patterns, you can make a statement with your outfit that proves you’re not afraid to stand above from the rest.


6. Winter Hipster Outfits

Winter Hipster Outfit The Freckled Princess
Source: @the_freckled_princess via Instagram

Ah, scarf season — the season most beloved by hipsters all around the world! It’s easy to make your trendy vibes shine in the snowy season through wardrobe items like long patterned peacoats, black tights, chunky turtlenecks, and more. To really pull off a cold weather look, don’t forget your trusty pair of boots — anywhere from ankle-length Chelsea boots to knee-level boots will work.